#------------------------------------------------------------------------------
#$Date: 2022-02-04 21:10:00 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272569 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/55/1565569.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1565569
loop_
_publ_author_name
'Timmermann, Christopher'
'Thiem, Paula'
'Wanitschke, Dominik'
'Hüttenschmidt, Mareike'
'Romischke, Johanna'
'Villinger, Alexander'
'Seidel, Wolfram W.'
_publ_section_title
;
 Migratory insertion of isocyanide into a ketenyl-tungsten bond as key
 step in cyclization reactions.
;
_journal_issue                   1
_journal_name_full               'Chemical science'
_journal_page_first              123
_journal_page_last               132
_journal_paper_doi               10.1039/d1sc06149f
_journal_volume                  13
_journal_year                    2021
_chemical_formula_moiety         'C23 H34 B Cl N6 O2 W, C H2 Cl2'
_chemical_formula_sum            'C24 H36 B Cl3 N6 O2 W'
_chemical_formula_weight         741.60
_chemical_name_systematic
'[Carbonyl-chlorido-η2-C,C?-ethinylethylether-hydridotris(3,4,5-trimethylpyrazolyl)borato-tungsten(II)]'
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2021-02-04 deposited with the CCDC.	2021-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                98.452(2)
_cell_angle_beta                 102.852(2)
_cell_angle_gamma                96.092(2)
_cell_formula_units_Z            2
_cell_length_a                   10.2936(4)
_cell_length_b                   11.0038(5)
_cell_length_c                   13.3415(5)
_cell_measurement_reflns_used    9742
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.91
_cell_measurement_theta_min      2.58
_cell_volume                     1442.14(10)
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_collection       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-2013
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Apex Kappa-II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1000
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            83572
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.999
_diffrn_reflns_theta_min         2.246
_exptl_absorpt_coefficient_mu    4.316
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane/n-pentane'
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_refine_diff_density_max         4.784
_refine_diff_density_min         -2.446
_refine_diff_density_rms         0.207
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         10022
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0327P)²+7.4348P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.0987
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8426
_reflns_number_total             10022
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc06149f2.cif
_cod_data_source_block           is_ct10741
_cod_depositor_comments
'Adding full bibliography for 1565569--1565576.cif.'
_cod_database_code               1565569
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.545
_shelx_estimated_absorpt_t_max   0.881
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
W1 W -0.10927(2) 0.19415(2) 0.18233(2) 0.01557(5) Uani 1 1 d . . . . .
B1 B 0.1840(5) 0.3769(4) 0.2770(3) 0.0149(8) Uani 1 1 d . . . . .
H1 H 0.2727 0.4318 0.3038 0.018 Uiso 1 1 calc R U . . .
Cl1 Cl -0.21993(12) 0.13622(10) 0.31566(8) 0.0240(2) Uani 1 1 d . . . . .
N1 N 0.0789(4) 0.1639(3) 0.2906(3) 0.0175(7) Uani 1 1 d . . . . .
N2 N 0.1901(3) 0.2532(3) 0.3185(3) 0.0161(6) Uani 1 1 d . . . . .
N3 N -0.0587(3) 0.3830(3) 0.2835(3) 0.0153(6) Uani 1 1 d . . . . .
N4 N 0.0718(3) 0.4408(3) 0.3135(3) 0.0155(6) Uani 1 1 d . . . . .
N5 N 0.0206(4) 0.2916(3) 0.1039(3) 0.0160(6) Uani 1 1 d . . . . .
N6 N 0.1463(3) 0.3516(3) 0.1569(3) 0.0158(6) Uani 1 1 d . . . . .
O1 O -0.3089(4) 0.0168(3) -0.0218(3) 0.0341(8) Uani 1 1 d . . . . .
O2 O -0.3637(4) 0.2770(4) 0.0565(3) 0.0371(9) Uani 1 1 d . . . . .
C1 C -0.2037(5) 0.0563(4) 0.0578(4) 0.0260(9) Uani 1 1 d . . . . .
C2 C -0.0942(6) 0.0240(4) 0.1046(4) 0.0268(10) Uani 1 1 d . . . . .
C3 C -0.3038(7) -0.1085(5) -0.0789(5) 0.0416(14) Uani 1 1 d . . . . .
H3A H -0.2168 -0.1101 -0.0988 0.050 Uiso 1 1 calc R U . . .
H3B H -0.3122 -0.1713 -0.0338 0.050 Uiso 1 1 calc R U . . .
C4 C -0.4152(6) -0.1364(5) -0.1725(4) 0.0372(12) Uani 1 1 d . . . . .
H4A H -0.5003 -0.1285 -0.1524 0.056 Uiso 1 1 calc R U . . .
H4B H -0.4180 -0.2214 -0.2083 0.056 Uiso 1 1 calc R U . . .
H4C H -0.4020 -0.0780 -0.2194 0.056 Uiso 1 1 calc R U . . .
C5 C -0.2707(5) 0.2503(5) 0.1048(4) 0.0254(9) Uani 1 1 d . . . . .
C6 C 0.1103(5) 0.0715(4) 0.3434(3) 0.0194(8) Uani 1 1 d . . . . .
C7 C 0.2410(5) 0.1021(4) 0.4066(3) 0.0212(8) Uani 1 1 d . . . . .
C8 C 0.2884(4) 0.2177(4) 0.3898(3) 0.0192(8) Uani 1 1 d . . . . .
C9 C 0.0185(5) -0.0460(4) 0.3349(4) 0.0292(10) Uani 1 1 d . . . . .
H9A H -0.0665 -0.0457 0.2843 0.044 Uiso 1 1 calc R U . . .
H9B H 0.0007 -0.0523 0.4033 0.044 Uiso 1 1 calc R U . . .
H9C H 0.0610 -0.1170 0.3117 0.044 Uiso 1 1 calc R U . . .
C10 C 0.3110(6) 0.0252(5) 0.4797(4) 0.0327(11) Uani 1 1 d . . . . .
H10A H 0.3985 0.0713 0.5192 0.049 Uiso 1 1 calc R U . . .
H10B H 0.3244 -0.0525 0.4395 0.049 Uiso 1 1 calc R U . . .
H10C H 0.2558 0.0065 0.5281 0.049 Uiso 1 1 calc R U . . .
C11 C 0.4213(5) 0.2949(5) 0.4382(4) 0.0284(10) Uani 1 1 d . . . . .
H11A H 0.4885 0.2410 0.4596 0.043 Uiso 1 1 calc R U . . .
H11B H 0.4145 0.3528 0.4994 0.043 Uiso 1 1 calc R U . . .
H11C H 0.4485 0.3418 0.3874 0.043 Uiso 1 1 calc R U . . .
C12 C -0.1324(4) 0.4615(4) 0.3255(3) 0.0170(7) Uani 1 1 d . . . . .
C13 C -0.0487(5) 0.5683(4) 0.3843(3) 0.0174(8) Uani 1 1 d . . . . .
C14 C 0.0790(4) 0.5523(4) 0.3740(3) 0.0169(7) Uani 1 1 d . . . . .
C15 C -0.2818(5) 0.4360(5) 0.3071(4) 0.0246(9) Uani 1 1 d . . . . .
H15A H -0.3240 0.4605 0.2412 0.037 Uiso 1 1 calc R U . . .
H15B H -0.3102 0.4835 0.3646 0.037 Uiso 1 1 calc R U . . .
H15C H -0.3094 0.3471 0.3035 0.037 Uiso 1 1 calc R U . . .
C16 C -0.0909(5) 0.6772(4) 0.4441(4) 0.0258(9) Uani 1 1 d . . . . .
H16A H -0.0111 0.7297 0.4906 0.039 Uiso 1 1 calc R U . . .
H16B H -0.1510 0.6476 0.4857 0.039 Uiso 1 1 calc R U . . .
H16C H -0.1382 0.7255 0.3952 0.039 Uiso 1 1 calc R U . . .
C17 C 0.2090(5) 0.6383(4) 0.4197(4) 0.0272(10) Uani 1 1 d . . . . .
H17A H 0.2787 0.5912 0.4503 0.041 Uiso 1 1 calc R U . . .
H17B H 0.1962 0.7030 0.4740 0.041 Uiso 1 1 calc R U . . .
H17C H 0.2368 0.6767 0.3646 0.041 Uiso 1 1 calc R U . . .
C18 C 0.0046(5) 0.3082(4) 0.0033(3) 0.0195(8) Uani 1 1 d . . . . .
C19 C 0.1199(5) 0.3792(4) -0.0075(3) 0.0225(9) Uani 1 1 d . . . . .
C20 C 0.2064(5) 0.4055(4) 0.0909(3) 0.0199(8) Uani 1 1 d . . . . .
C21 C -0.1195(5) 0.2590(5) -0.0806(4) 0.0288(10) Uani 1 1 d . . . . .
H21A H -0.1313 0.1680 -0.0932 0.043 Uiso 1 1 calc R U . . .
H21B H -0.1113 0.2889 -0.1449 0.043 Uiso 1 1 calc R U . . .
H21C H -0.1977 0.2876 -0.0590 0.043 Uiso 1 1 calc R U . . .
C22 C 0.1378(6) 0.4220(5) -0.1056(4) 0.0352(12) Uani 1 1 d . . . . .
H22A H 0.2302 0.4635 -0.0945 0.053 Uiso 1 1 calc R U . . .
H22B H 0.0745 0.4802 -0.1243 0.053 Uiso 1 1 calc R U . . .
H22C H 0.1204 0.3503 -0.1623 0.053 Uiso 1 1 calc R U . . .
C23 C 0.3453(5) 0.4777(5) 0.1234(4) 0.0297(10) Uani 1 1 d . . . . .
H23A H 0.3541 0.5370 0.1878 0.045 Uiso 1 1 calc R U . . .
H23B H 0.3610 0.5228 0.0681 0.045 Uiso 1 1 calc R U . . .
H23C H 0.4117 0.4206 0.1356 0.045 Uiso 1 1 calc R U . . .
H2 H -0.050(9) -0.027(8) 0.102(7) 0.07(3) Uiso 1 1 d . . . . .
C24 C 0.5383(6) 0.8596(6) 0.1927(5) 0.0419(13) Uani 1 1 d . . . . .
H24A H 0.4847 0.8662 0.1227 0.050 Uiso 1 1 calc R U . . .
H24B H 0.5932 0.9414 0.2240 0.050 Uiso 1 1 calc R U . . .
Cl2 Cl 0.4282(2) 0.8228(2) 0.27148(15) 0.0636(5) Uani 1 1 d . . . . .
Cl3 Cl 0.6454(2) 0.7485(2) 0.1791(2) 0.0752(6) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 W1 C2 107.7(2) . . ?
C5 W1 C1 71.6(2) . . ?
C2 W1 C1 36.2(2) . . ?
C5 W1 N5 92.65(16) . . ?
C2 W1 N5 93.19(17) . . ?
C1 W1 N5 97.29(17) . . ?
C5 W1 N1 169.32(16) . . ?
C2 W1 N1 82.96(18) . . ?
C1 W1 N1 119.08(17) . . ?
N5 W1 N1 86.56(13) . . ?
C5 W1 N3 87.84(16) . . ?
C2 W1 N3 162.75(18) . . ?
C1 W1 N3 158.84(17) . . ?
N5 W1 N3 78.32(12) . . ?
N1 W1 N3 81.57(13) . . ?
C5 W1 Cl1 92.90(14) . . ?
C2 W1 Cl1 101.32(15) . . ?
C1 W1 Cl1 100.63(14) . . ?
N5 W1 Cl1 162.08(9) . . ?
N1 W1 Cl1 84.85(10) . . ?
N3 W1 Cl1 84.87(9) . . ?
N6 B1 N2 110.1(3) . . ?
N6 B1 N4 107.6(3) . . ?
N2 B1 N4 108.4(3) . . ?
N6 B1 H1 110.2 . . ?
N2 B1 H1 110.2 . . ?
N4 B1 H1 110.2 . . ?
C6 N1 N2 106.7(3) . . ?
C6 N1 W1 132.9(3) . . ?
N2 N1 W1 120.4(3) . . ?
C8 N2 N1 109.8(3) . . ?
C8 N2 B1 130.2(4) . . ?
N1 N2 B1 119.8(3) . . ?
C12 N3 N4 106.4(3) . . ?
C12 N3 W1 133.7(3) . . ?
N4 N3 W1 119.9(3) . . ?
C14 N4 N3 109.8(3) . . ?
C14 N4 B1 130.0(3) . . ?
N3 N4 B1 120.1(3) . . ?
C18 N5 N6 106.6(3) . . ?
C18 N5 W1 132.2(3) . . ?
N6 N5 W1 121.2(2) . . ?
C20 N6 N5 109.7(3) . . ?
C20 N6 B1 128.6(4) . . ?
N5 N6 B1 119.8(3) . . ?
C1 O1 C3 112.9(4) . . ?
C2 C1 O1 141.5(5) . . ?
C2 C1 W1 71.2(3) . . ?
O1 C1 W1 147.3(4) . . ?
C1 C2 W1 72.6(3) . . ?
C1 C2 H2 143(7) . . ?
W1 C2 H2 145(7) . . ?
C4 C3 O1 108.2(5) . . ?
C4 C3 H3A 110.1 . . ?
O1 C3 H3A 110.1 . . ?
C4 C3 H3B 110.1 . . ?
O1 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O2 C5 W1 176.3(4) . . ?
N1 C6 C7 109.9(4) . . ?
N1 C6 C9 124.8(4) . . ?
C7 C6 C9 125.4(4) . . ?
C8 C7 C6 105.8(4) . . ?
C8 C7 C10 128.1(4) . . ?
C6 C7 C10 126.0(4) . . ?
N2 C8 C7 107.9(4) . . ?
N2 C8 C11 123.6(4) . . ?
C7 C8 C11 128.6(4) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C13 110.0(4) . . ?
N3 C12 C15 123.4(4) . . ?
C13 C12 C15 126.6(4) . . ?
C14 C13 C12 105.4(4) . . ?
C14 C13 C16 127.9(4) . . ?
C12 C13 C16 126.7(4) . . ?
N4 C14 C13 108.4(4) . . ?
N4 C14 C17 122.8(4) . . ?
C13 C14 C17 128.8(4) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N5 C18 C19 109.7(4) . . ?
N5 C18 C21 124.0(4) . . ?
C19 C18 C21 126.3(4) . . ?
C20 C19 C18 105.6(4) . . ?
C20 C19 C22 128.8(5) . . ?
C18 C19 C22 125.5(5) . . ?
N6 C20 C19 108.4(4) . . ?
N6 C20 C23 123.5(4) . . ?
C19 C20 C23 128.1(4) . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
Cl3 C24 Cl2 112.3(4) . . ?
Cl3 C24 H24A 109.1 . . ?
Cl2 C24 H24A 109.1 . . ?
Cl3 C24 H24B 109.1 . . ?
Cl2 C24 H24B 109.1 . . ?
H24A C24 H24B 107.9 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
W1 C5 1.963(5) . ?
W1 C2 2.041(5) . ?
W1 C1 2.057(5) . ?
W1 N5 2.163(3) . ?
W1 N1 2.232(4) . ?
W1 N3 2.246(3) . ?
W1 Cl1 2.4390(11) . ?
B1 N6 1.537(6) . ?
B1 N2 1.545(5) . ?
B1 N4 1.546(6) . ?
B1 H1 1.0000 . ?
N1 C6 1.346(5) . ?
N1 N2 1.371(5) . ?
N2 C8 1.358(5) . ?
N3 C12 1.350(5) . ?
N3 N4 1.369(5) . ?
N4 C14 1.351(5) . ?
N5 C18 1.357(5) . ?
N5 N6 1.373(5) . ?
N6 C20 1.352(5) . ?
O1 C1 1.320(6) . ?
O1 C3 1.486(6) . ?
O2 C5 1.121(6) . ?
C1 C2 1.274(7) . ?
C2 H2 0.76(9) . ?
C3 C4 1.464(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C6 C7 1.397(6) . ?
C6 C9 1.492(6) . ?
C7 C8 1.381(6) . ?
C7 C10 1.498(6) . ?
C8 C11 1.486(6) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.397(6) . ?
C12 C15 1.491(6) . ?
C13 C14 1.379(6) . ?
C13 C16 1.499(6) . ?
C14 C17 1.502(6) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.397(6) . ?
C18 C21 1.489(6) . ?
C19 C20 1.384(6) . ?
C19 C22 1.496(6) . ?
C20 C23 1.499(7) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 Cl3 1.746(6) . ?
C24 Cl2 1.764(7) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 N2 C8 -1.4(5) . . . . ?
W1 N1 N2 C8 176.0(3) . . . . ?
C6 N1 N2 B1 -175.9(4) . . . . ?
W1 N1 N2 B1 1.5(5) . . . . ?
N6 B1 N2 C8 128.9(4) . . . . ?
N4 B1 N2 C8 -113.7(4) . . . . ?
N6 B1 N2 N1 -57.9(5) . . . . ?
N4 B1 N2 N1 59.6(5) . . . . ?
C12 N3 N4 C14 0.7(4) . . . . ?
W1 N3 N4 C14 -179.7(3) . . . . ?
C12 N3 N4 B1 -178.9(3) . . . . ?
W1 N3 N4 B1 0.6(4) . . . . ?
N6 B1 N4 C14 -121.3(4) . . . . ?
N2 B1 N4 C14 119.7(4) . . . . ?
N6 B1 N4 N3 58.2(4) . . . . ?
N2 B1 N4 N3 -60.8(4) . . . . ?
C18 N5 N6 C20 0.6(4) . . . . ?
W1 N5 N6 C20 -179.6(3) . . . . ?
C18 N5 N6 B1 165.9(3) . . . . ?
W1 N5 N6 B1 -14.4(5) . . . . ?
N2 B1 N6 C20 -131.3(4) . . . . ?
N4 B1 N6 C20 110.8(4) . . . . ?
N2 B1 N6 N5 66.6(4) . . . . ?
N4 B1 N6 N5 -51.3(4) . . . . ?
C3 O1 C1 C2 0.7(10) . . . . ?
C3 O1 C1 W1 -177.8(6) . . . . ?
O1 C1 C2 W1 -179.2(8) . . . . ?
C1 O1 C3 C4 -173.0(5) . . . . ?
N2 N1 C6 C7 1.0(5) . . . . ?
W1 N1 C6 C7 -176.0(3) . . . . ?
N2 N1 C6 C9 -179.0(4) . . . . ?
W1 N1 C6 C9 4.1(7) . . . . ?
N1 C6 C7 C8 -0.2(5) . . . . ?
C9 C6 C7 C8 179.7(4) . . . . ?
N1 C6 C7 C10 178.0(4) . . . . ?
C9 C6 C7 C10 -2.1(8) . . . . ?
N1 N2 C8 C7 1.3(5) . . . . ?
B1 N2 C8 C7 175.0(4) . . . . ?
N1 N2 C8 C11 -178.5(4) . . . . ?
B1 N2 C8 C11 -4.8(7) . . . . ?
C6 C7 C8 N2 -0.6(5) . . . . ?
C10 C7 C8 N2 -178.8(5) . . . . ?
C6 C7 C8 C11 179.2(5) . . . . ?
C10 C7 C8 C11 1.0(8) . . . . ?
N4 N3 C12 C13 -1.3(4) . . . . ?
W1 N3 C12 C13 179.2(3) . . . . ?
N4 N3 C12 C15 177.0(4) . . . . ?
W1 N3 C12 C15 -2.5(6) . . . . ?
N3 C12 C13 C14 1.4(4) . . . . ?
C15 C12 C13 C14 -176.8(4) . . . . ?
N3 C12 C13 C16 -179.4(4) . . . . ?
C15 C12 C13 C16 2.4(7) . . . . ?
N3 N4 C14 C13 0.1(4) . . . . ?
B1 N4 C14 C13 179.7(4) . . . . ?
N3 N4 C14 C17 179.8(4) . . . . ?
B1 N4 C14 C17 -0.6(7) . . . . ?
C12 C13 C14 N4 -0.9(4) . . . . ?
C16 C13 C14 N4 179.9(4) . . . . ?
C12 C13 C14 C17 179.5(4) . . . . ?
C16 C13 C14 C17 0.2(7) . . . . ?
N6 N5 C18 C19 -0.2(5) . . . . ?
W1 N5 C18 C19 -179.9(3) . . . . ?
N6 N5 C18 C21 -179.2(4) . . . . ?
W1 N5 C18 C21 1.2(6) . . . . ?
N5 C18 C19 C20 -0.3(5) . . . . ?
C21 C18 C19 C20 178.6(4) . . . . ?
N5 C18 C19 C22 -177.0(4) . . . . ?
C21 C18 C19 C22 2.0(7) . . . . ?
N5 N6 C20 C19 -0.8(5) . . . . ?
B1 N6 C20 C19 -164.4(4) . . . . ?
N5 N6 C20 C23 -179.4(4) . . . . ?
B1 N6 C20 C23 17.0(7) . . . . ?
C18 C19 C20 N6 0.7(5) . . . . ?
C22 C19 C20 N6 177.2(5) . . . . ?
C18 C19 C20 C23 179.2(4) . . . . ?
C22 C19 C20 C23 -4.3(8) . . . . ?
